Chemical synthesis of 6′-α-maltosyl-maltotriose, a branched oligosaccharide representing the branch point of starch

Motawia, Mohammed Saddik; Olsen, Carl Erik; Enevoldsen, K.; Marcussen, Jan; Møller, Birger Lindberg

doi:10.1016/0008-6215(95)00203-6

Cited by 50 publications

(53 citation statements)

References 25 publications

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“…In this strategy, D-glucose (1) was converted into phenyl 2,3,4,6-tetra-O-acetyl-1-thio-b-D-glucopyranoside (3) as described by literature. 26 The commercially available methyl b-D-glycopyranoside (2) was manipulated and converted into both methyl 2,3,6-O-benzyl-b-D-glucopyranoside (4) 27 and methyl 2,4,6-O-benzyol-b-Dglucopyranoside (5) 28 according to the reported procedures. Glycosidation reaction between the phenylthio glucopyranoside derivative 3 as a glycosyl donor using the methyl glucopyranoside derivative 4 or 5 as the glycosyl acceptors with the activator NISTfOH system 29 provided the corresponding disaccharide derivatives 6 and 7.…”

Section: Synthesis Of Methyl B-cellobioside and Methyl Blaminarabiosidementioning

confidence: 99%

A combined nuclear magnetic resonance and molecular dynamics study of the two structural motifs for mixed-linkage β-glucans: methyl β-cellobioside and methyl β-laminarabioside

Christensen¹,

Pb²,

Larsen³

et al. 2010

Carbohydrate Research

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Section: Synthesis Of Methyl B-cellobioside and Methyl Blaminarabiosidementioning

confidence: 99%

A combined nuclear magnetic resonance and molecular dynamics study of the two structural motifs for mixed-linkage β-glucans: methyl β-cellobioside and methyl β-laminarabioside

Christensen¹,

Pb²,

Larsen³

et al. 2010

Carbohydrate Research

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“…26 Glucopyranoside donor 9 was synthesized from thiophenyl β‐glucopyranoside 8 27. While 4,6‐silylidene protection proceeded smoothly, elevated temperatures were required to install the TBS‐groups onto both secondary hydroxyl groups, presumably due to steric hindrance.…”

Section: Resultsmentioning

confidence: 99%

“…(4 aR ,6 S ,7 R ,8 S ,8 aR )‐2,2‐Di‐ tert ‐butyl‐7,8‐bis(( tert ‐butyldimethylsilyl)oxy)‐6‐(phenylthio)hexahydropyrano[3,2‐ d ][1,3,2]dioxasiline (9) : Compound 8 27 (2.6 g, 9.5 mmol) was dissolved in dry DMF (100 mL) under Ar‐atmosphere. The mixture was cooled to −50 °C and 2,6‐lutidine (3.3 mL, 28.5 mmol) and Si t Bu 2 (OTf) 2 (3.4 mL, 10.5 mmol) was added.…”

Section: Methodsmentioning

confidence: 99%

Spiro‐epoxyglycosides as Activity‐Based Probes for Glycoside Hydrolase Family 99 Endomannosidase/Endomannanase

Schröder

Kallemeijn²,

Debets

et al. 2018

Chemistry A European J

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N‐Glycans direct protein function, stability, folding and targeting, and influence immunogenicity. While most glycosidases that process N‐glycans cleave a single sugar residue at a time, enzymes from glycoside hydrolase family 99 are endo‐acting enzymes that cleave within complex N‐glycans. Eukaryotic Golgi endo‐1,2‐α‐mannosidase cleaves glucose‐substituted mannose within immature glucosylated high‐mannose N‐glycans in the secretory pathway. Certain bacteria within the human gut microbiota produce endo‐1,2‐α‐mannanase, which cleaves related structures within fungal mannan, as part of nutrient acquisition. An unconventional mechanism of catalysis was proposed for enzymes of this family, hinted at by crystal structures of imino/azasugars complexed within the active site. Based on this mechanism, we developed the synthesis of two glycosides bearing a spiro‐epoxide at C‐2 as electrophilic trap, to covalently bind a mechanistically important, conserved GH99 catalytic residue. The spiro‐epoxyglycosides are equipped with a fluorescent tag, and following incubation with recombinant enzyme, allow concentration, time and pH dependent visualization of the bound enzyme using gel electrophoresis.

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“…This downfield shift of C resonance was confirmed by previous research. [4,20] In addition, the PREPARATION HMBC spectra allowed for determination of the order of the branched point. As shown in Fig.…”

Section: Effect Of Temperature On the Preparation Of 6 2 −α-Maltotriomentioning

confidence: 99%

“…Multifarious protections and de-protection strategies are essential for the achievement of the desired oligosaccharides. [4,5] These complicated processes cause limitations to the application and research of oligosaccharides. Enzymatic synthesis of oligosaccharides is a promising alternative to the chemical method.…”

Section: Introductionmentioning

confidence: 99%

Preparation and Identification of 6²−α-Maltotriosyl-Maltotriose Using a Commercial Pullulanase

Bai

et al. 2014

International Journal of Food Properties

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In this article, 6 2 −α-maltotriosyl-maltotriose was consecutively prepared by hydrolysis and reverse synthesis action of Bacillus Acidopullulyticus pullulanase using pullulan as a substrate. Maltotriose syrup was obtained by hydrolyzing of pullulan with pullulanase. The optimal reverse synthesis conditions were then investigated and the optimum conditions were as follows: maltotriose syrup concentration, 70-75%; time, 40 h; pH, 4.0; temperature, 65 • C; amount of pullulanase, 120 U. Under these conditions, the relative conversion rate of reverse synthesis reached up to 26%. The products were further isolated by preparative high performance liquid chromatography on Lichrospher NH 2 column. 6 2 −α-Maltotriosyl-maltotriose was purified and maltotriose syrup was collected and recycled as the substrate for reverse synthesis. Structure of 6 2 −α-maltotriosyl-maltotriose was elucidated by electrospray ionization mass spectrometry, fourier transform infrared spectroscopy, 1 H nuclear magnetic resonance, 13 C nuclear magnetic resonance, and heteronuclear multiple bond correlation. These results suggested that this was a promising way of preparation of 6 2 −α-maltotriosyl-maltotriose.

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Chemical synthesis of 6′-α-maltosyl-maltotriose, a branched oligosaccharide representing the branch point of starch

Cited by 50 publications

References 25 publications

A combined nuclear magnetic resonance and molecular dynamics study of the two structural motifs for mixed-linkage β-glucans: methyl β-cellobioside and methyl β-laminarabioside

A combined nuclear magnetic resonance and molecular dynamics study of the two structural motifs for mixed-linkage β-glucans: methyl β-cellobioside and methyl β-laminarabioside

Spiro‐epoxyglycosides as Activity‐Based Probes for Glycoside Hydrolase Family 99 Endomannosidase/Endomannanase

Preparation and Identification of 6²−α-Maltotriosyl-Maltotriose Using a Commercial Pullulanase

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Chemical synthesis of 6′-α-maltosyl-maltotriose, a branched oligosaccharide representing the branch point of starch

Cited by 50 publications

References 25 publications

A combined nuclear magnetic resonance and molecular dynamics study of the two structural motifs for mixed-linkage β-glucans: methyl β-cellobioside and methyl β-laminarabioside

A combined nuclear magnetic resonance and molecular dynamics study of the two structural motifs for mixed-linkage β-glucans: methyl β-cellobioside and methyl β-laminarabioside

Spiro‐epoxyglycosides as Activity‐Based Probes for Glycoside Hydrolase Family 99 Endomannosidase/Endomannanase

Preparation and Identification of 62−α-Maltotriosyl-Maltotriose Using a Commercial Pullulanase

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Preparation and Identification of 6²−α-Maltotriosyl-Maltotriose Using a Commercial Pullulanase